Pyridine → HCID 57682687, compound

HRID 494221Notes

Reaction equation

HRID 494221 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2[CH2:12][CH2:13][N:14]([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])=[CH:4][CH:3]=1.[C:21]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:26]=[CH:25][C:24]([C:27](Cl)=[O:28])=[CH:23][CH:22]=1.N1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH:15]([N:14]([CH:18]([CH3:20])[CH3:19])[CH2:13][CH2:12][N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:27]([C:24]3[CH:25]=[CH:26][C:21]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:22][CH:23]=3)=[O:28])[CH:11]=2)[CH2:6][CH2:7][CH2:8]1)([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 841514-Phenylbenzoyl chlorideHCID 54457265HCID 54457265, compound

Product 1

HCID 57682687HCID 57682687, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Amino-1-(2-diisopropylaminoethyl)-1,2,3,4-tetrahydroquinoline (D15) (100 mg, 0.36 mmol), 4-biphenylcarbonyl chloride (258 mg, 1.11 mmol) and pyridine (0.5 ml, 6.2 mmol) in DCM (5 ml) were stirred at room temperatue for 4 hours. 10% Potassium carbonate solution was then added and the mixture extracted with DCM which was dried over MgSO4 and concentrated in vacuo to give the crude product. Purification by flash column chromatography eluting with 0-5% methanol/DCM gave the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.92 (d, 2H), 7.71 (d, 2H), 7.63 (m, 3H), 7.47 (t, 2H), 7.41 (t, 1H), 6.99 (br, 1H), 6.90 (d, 1H), 6.74 (d, 1H), 3.37 (m, 2H), 3.30 (m, 2H), 3.05 (sp, 2H), 2.72 (t, 2H), 2.66 (m, 2H), 1.93 (m, 2H), 1.05 (d, 12H).

Workup

  1. extractionthe mixture extracted with DCM which
  2. dry with materialwas dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give the crude product
  5. customPurification by flash column chromatography
  6. washeluting with 0-5% methanol/DCM

Sources & evidence

ORD record
ord-6db7b9d9f9564151bcbe67c2931d6650
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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